Issue 5, 2017

Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

Abstract

Dibenzo[a,e]pentalene (DBP) is a low-bandgap organic semiconductor. A versatile synthetic route to DBPs substituted with aryl or alkyl groups in the 5,10-positions and electron-donating or -accepting functionalities in the 2,7-positions is described. Six donor- or acceptor-functionalized DBP derivatives were synthesized that show amphoteric redox behavior and band gaps around 2 eV. Through choice of the 2,7-substituents, the HOMO/LUMO energy levels and band gaps can be adjusted within a range of up to 0.6 eV. In the solid state, the DBP derivatives assume herringbone-type packing structures.

Graphical abstract: Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

Supplementary files

Article information

Article type
Research Article
Submitted
24 avg 2016
Accepted
26 sep 2016
First published
27 sep 2016
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2017,4, 658-663

Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

J. Wilbuer, D. C. Grenz, G. Schnakenburg and B. Esser, Org. Chem. Front., 2017, 4, 658 DOI: 10.1039/C6QO00487C

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